Piperidine → HCID 57114861, compound

HRID 384469Notes

Reaction equation

[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11](Br)[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1(P(C2CCCCC2)C2C=CC=CC=2C2[C:30]([N:35]([CH3:37])C)=[CH:31][CH:32]=[CH:33]C=2)CCCCC1.N1CCCCC1.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>COCCOC.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([N:35]2[CH2:30][CH2:31][CH2:32][CH2:33][CH2:37]2)[CH:12]=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 110 °C

Procedure

To a solution of 1-(benzyloxy)-3-bromobenzene (1.00 g) in 1,2-dimethoxyethane (15 mL) were added tris(dibenzylideneacetone)dipalladium(0) (180 mg), 2′-[dicyclohexylphosphino]-N,N-dimethylbiphenyl-2-amine (150 mg), piperidine (500 μL), and tripotassium phosphate (2.5 g) at room temperature, and the mixture was stirred at 110° C. for 21 hours. After the reaction mixture was cooled to room temperature, insolubles were separated by filtration and the solvent was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=100/0-85/15) to obtain 1-[3-(benzyloxy)phenyl]piperidine (722 mg).

Workup

temperatureAfter the reaction mixture was cooled to room temperature
custominsolubles were separated by filtration
concentrationthe solvent was concentrated under reduced pressure
customThe residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=100/0-85/15)

Sources & evidence

ORD record: ord-0cdcde76b0334ae29a05a4fc6da019a3
Source dataset: uspto-grants-2013_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08367702B2

Reaction notes

Loading…